Details of the Drug

General Information of Drug (ID: DMWH7NQ)

Drug Name
Alprostadil
Synonyms
Prostaglandin E1; alprostadil; 745-65-3; PGE1; Muse; Edex; Caverject; Prostin VR; Alprostadilum; Femprox; Befar; Vitaros; Prostandin; Liprostin; PGE-1; Prink (TN); Befar (TN); Prostavasin; Vasaprostan; MR-256; Minprog; UNII-F5TD010360; Alprostadil(Caverject); CHEMBL495; (11alpha,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid; Prostivas; Lipoprost; 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid; (13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate; FemLife; RayVa; Sugiran; Viridal; MR 256; PGE1 Oligomer; BML1-F06; Caverject (TN); Edex (TN); HEI-507; Muse (TN); Prostin VR pediatric (TN); U-10136; Alprostadil (JP15/USP/INN); Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11alpha,13E,15S)-, homopolymer; (11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid; (13E,15S)-11alpha,15-dihydroxy-9-oxoprost-13-en-1-oic acid; 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid; Lipo-alprostadil
Indication
Disease Entry ICD 11 Status REF
Aorta coarctation N.A. Approved [1]
Diabetic foot ulcer BD54 Approved [2]
Erectile dysfunction HA01.1 Approved [3]
Pulmonary hypertension BB01 Approved [1]
Tetralogy of fallot N.A. Approved [1]
Therapeutic Class
Vasodilator Agents
Affected Organisms
Humans and other mammals
ATC Code
C01EA01: Alprostadil
C01EA: Prostaglandins
C01E: OTHER CARDIAC PREPARATIONS
C01: CARDIAC THERAPY
C: CARDIOVASCULAR SYSTEM
G04BE01: Alprostadil
G04BE: Drugs used in erectile dysfunction
G04B: UROLOGICALS
G04: UROLOGICALS
G: GENITO URINARY SYSTEM AND SEX HORMONES
G04BE01: Alprostadil
G04BE: Drugs used in erectile dysfunction
G04B: UROLOGICALS
G04: UROLOGICALS
G: GENITO URINARY SYSTEM AND SEX HORMONES
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 354.5
Logarithm of the Partition Coefficient (xlogp) 3.2
Rotatable Bond Count (rotbonds) 13
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 45.4 mL/min/kg [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 5 - 10 minutes [4]
Metabolism
The drug is metabolized via the lung []
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 2.4 L/kg [4]
Chemical Identifiers
Formula
C20H34O5
IUPAC Name
7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
Canonical SMILES
CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O
InChI
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
InChIKey
GMVPRGQOIOIIMI-DWKJAMRDSA-N
Cross-matching ID
PubChem CID
5280723
ChEBI ID
CHEMBL495
CAS Number
745-65-3
UNII
F5TD010360
DrugBank ID
DB00770
TTD ID
D0I4DQ
VARIDT ID
DR00210
INTEDE ID
DR1923
ACDINA ID
D00828
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin E2 receptor EP2 (PTGER2) TT1ZAVI PE2R2_HUMAN Agonist [2]
Thromboxane A2 receptor (TBXA2R) TT2O84V TA2R_HUMAN Modulator [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporting polypeptide 2A1 (SLCO2A1) DT021JD SO2A1_HUMAN Substrate [6]
Organic anion transporting polypeptide 3A1 (SLCO3A1) DTVNRXW SO3A1_HUMAN Substrate [7]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [8]
Organic anion transporter 1 (SLC22A6) DTQ23VB S22A6_HUMAN Substrate [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Prostaglandin dehydrogenase 1 (HPGD)
Main DME 		DEHKSC6 PGDH_HUMAN Substrate [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Post-Translational Modifications [11]
Natriuretic peptides A (NPPA) OTMQNTNX ANF_HUMAN Gene/Protein Processing [12]
Natriuretic peptides B (NPPB) OTSN2IPY ANFB_HUMAN Gene/Protein Processing [13]
Renin (REN) OT52GZR2 RENI_HUMAN Gene/Protein Processing [14]
Vasodilator-stimulated phosphoprotein OTFC3010 VASP_HUMAN Post-Translational Modifications [15]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Aorta coarctation
ICD Disease Classification
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin E2 receptor EP2 (PTGER2) DTT PTGER2 2.77E-06 1.15 1.37
Organic anion transporting polypeptide 3A1 (SLCO3A1) DTP OATP3A1 9.66E-01 2.27E-01 3.78E-01
Organic anion transporter 1 (SLC22A6) DTP OAT1 7.57E-01 6.84E-02 1.89E-01
Multidrug resistance-associated protein 4 (ABCC4) DTP MRP4 3.78E-01 -2.23E-02 -1.90E-02
Organic anion transporting polypeptide 2A1 (SLCO2A1) DTP OATP2A1 6.15E-01 -3.02E-02 -2.83E-02
Prostaglandin dehydrogenase 1 (HPGD) DME HPGD 8.89E-04 -1.60E+00 -7.87E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Alprostadil (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Ardeparin DMYRX8B Moderate Increased risk of bleeding by the combination of Alprostadil and Ardeparin. Coronary thrombosis [BA43] [16]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Benzyl alcohol E00010 244 Antimicrobial preservative; Solvent
Hydrochloric acid E00015 313 Acidulant
Sodium citrate anhydrous E00102 6224 Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Alfadex E00419 444913 Other agent
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Sodium chloride E00077 5234 Diluent; Tonicity agent
Sodium hydroxide E00234 14798 Alkalizing agent
⏷ Show the Full List of 7 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Alprostadil 0.01mg/vial injectable 0.01mg/vial Injectable Injection
Alprostadil 0.005mg/vial injectable 0.005mg/vial Injectable Injection
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Alprostadil FDA Label
2 Emerging drugs for diabetic foot ulcers. Expert Opin Emerg Drugs. 2006 Nov;11(4):709-24.
3 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1882).
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Flow after prostaglandin E1 is mediated by receptor-coupled adenylyl cyclase in human anterior segments. Invest Ophthalmol Vis Sci. 1999 Oct;40(11):2622-6.
6 Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9.
7 Molecular characterization of human and rat organic anion transporter OATP-D. Am J Physiol Renal Physiol. 2003 Dec;285(6):F1188-97.
8 The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9.
9 Prostaglandin transporter (OATP2A1/SLCO2A1) contributes to local disposition of eicosapentaenoic acid-derived PGE3. Prostaglandins Other Lipid Mediat. 2016 Jan;122:10-7.
10 Effect of calcium ionophore A23187 on prostaglandin synthase type 2 and 15-hydroxy-prostaglandin dehydrogenase expression in human chorion trophoblast cells. Am J Obstet Gynecol. 2008 Nov;199(5):554.e1-8.
11 Characterization of agonist stimulation of cAMP-dependent protein kinase and G protein-coupled receptor kinase phosphorylation of the beta2-adrenergic receptor using phosphoserine-specific antibodies. Mol Pharmacol. 2004 Jan;65(1):196-206. doi: 10.1124/mol.65.1.196.
12 Effects of prostaglandin E1, dobutamine and placebo on hemodynamic, renal and neurohumoral variables in patients with advanced heart failure. Jpn Heart J. 1999 May;40(3):321-34. doi: 10.1536/jhj.40.321.
13 Short-term effects of levosimendan and prostaglandin E1 on hemodynamic parameters and B-type natriuretic peptide levels in patients with decompensated chronic heart failure. Eur J Heart Fail. 2005 Dec;7(7):1156-63. doi: 10.1016/j.ejheart.2005.05.001. Epub 2005 Aug 5.
14 Catecholamine and renin-angiotensin response during controlled hypotension induced by prostaglandin E1 combined with hemodilution during isoflurane anesthesia. J Clin Anesth. 1997 Jun;9(4):321-7. doi: 10.1016/s0952-8180(97)00011-1.
15 Arsenic trioxide-mediated antiplatelet activity: pivotal role of the phospholipase C gamma 2-protein kinase C-p38 MAPK cascade. Transl Res. 2010 Feb;155(2):97-108. doi: 10.1016/j.trsl.2009.08.005. Epub 2009 Sep 15.
16 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".